MCQ
Two compounds $A$ and $B$ with same molecular formula $\left( C _{3} H _{6} O \right)$ undergo Grignard's reaction with methylmagnesium bromide to give products $C$ and $D$. products $C$ and $D$ show following chemical tests.

Test $C$ $D$
Ceric ammonium nitrate Test Positive positive
Lucas Test Turbidity obtained after five minutes Turbidity obtained immediately
Iodoform Test Positive Negative

$C$ and $D$ respectively are 

  • A
    $C = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3\,\,\,\,\,\,\,\,}} \end{array}$

    $\begin{array}{*{20}{c}} {D = {H_3}C - C{H_2} - CH - C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \end{array}$

  • B
    $C = H _{3} C - CH _{2}- C H _{2}- CH _{2}- OH$

    $D = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3}\,\,\,\,\,} \end{array}$

  • $\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C = {H_3}C - C{H_2} - CH - C{H_3}} \end{array}$

    $D = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3}\,\,\,\,\,} \end{array}$

  • D
    $C = H _{3} C - CH _{2}- CH _{2}- CH _{2}- OH$

    $\begin{array}{*{20}{c}} {D = {H_3}C - C{H_2} - CH - C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \end{array}$

Answer

Correct option: C.
$\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C = {H_3}C - C{H_2} - CH - C{H_3}} \end{array}$

$D = {H_3}C - \begin{array}{*{20}{c}} {C{H_3}\,\,\,\,\,} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C - OH} \\ |\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {C{H_3}\,\,\,\,\,} \end{array}$

c
$\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,O} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,||} \\ {C{H_3}C - C{H_2} - C - H} \\ {(A)} \end{array}$ $\xrightarrow{CH_3MgBr}$$\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\ {C{H_3} - C{H_2} - CH - C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,{2^o}\,Alcohol} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\left( C \right)} \end{array}$

$CAN$ test for alcohol : $(yes)$

Iodoform test $:(yes)$

$\begin{array}{*{20}{c}} O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\ {||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ {C{H_3} - C - C{H_3}\,\xrightarrow{{C{H_3}MgBr}}} \\ {(B)\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\ {} \end{array}$$\begin{array}{*{20}{c}} {\,\,\,\,\,\,\,OH} \\ | \\ {C{H_3} - C - C{H_3}} \\ | \\ {\,\,\,\,\,\,\,\,C{H_3}} \\ {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,{3^o}\,Alcohol} \end{array}$

$CAN$ test for alcohol : $(yes)$

Lucas test : Immediately

Iodoform test : $(no)$

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